Collect. Czech. Chem. Commun. 1991, 56, 1032-1036

Enantioselective addition of optically active organotitanium reagents to benzaldehyde

Otakar Červinka, Marcel Pátek and Vladimír Stružka

Department of Organic Chemistry, Prague Institute of Technology, 166 28 Prague 6


Addition of optically active alkyltitanium (IV) reagents IIb and IIc to benzaldehyde afforded optically active 1-phenylethanol (V) of 37-48% optical purity and 1-phenylpentanol (VI) of 10-24% optical purity. Reagents IIb and IIc were prepared with the use of (1R,2S)-(-)-1-phenyl-1,2-propanediol (III) and (1R,2S)-(+)-1-cyclohexyl-1,2-propanediol (IV) as optically active components. Relations between the enantioselectivity achieved and reaction conditions are discussed.